My New Friend Amy Ch. 03

As I drove home that evening I had the replay of the days events running on a loop in my mind. I can't believe I paraded around in panties at lingerie store in front of strange women at the instruction of my new mistress. Hell, I signed a contract to obey her no matter what she says! Then I begged to jack off in front of her. I'm even a panty wearing sissy now! A few days ago I never would have imagined this would be reality for me.

My wife and I have separate closets so I decided that would be a good place to hide my new stack panties. I always thought thongs would be uncomfortable but truthfully you don't even feel the butt floss part much at all unless you focus on it. I'd like to feel bad for what I'm doing since I'm married but honestly I don't. I don't plan to have sex with any women, my wife isn't into my humiliation fetish, I will still provide well for her and my kids, and I will still give Kathleen sex as often as she wants which tends to be bi-monthly. This is a win/win in my book.

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I woke up early the next morning before my 5:30 alarm went off. I like to work out a little in the morning before I head to work. While getting dressed in the bathroom I noticed I had a text notification on my phone so I opened it up. It was sent from Amy at 3am.

"Now this is what a real man wields between his legs sissy." The text read and included a picture of her kissing the head of a fairly big cock. I'd guess that was Jake. He must have an 8 or 9 inch thick cock with big manly looking balls. He had hair down there but it was groomed nicely. That made me feel even more sissified since Amy told me I have to stay smooth on my cock, balls, and asshole. I can't lie, I got hard wondering what it would be like to kneel in front of Jake in nothing but panties and kiss his dick while Amy degrades me. I had to stroke my little dick to orgasm immediately.

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"Send me a picture of your little dick right now. My mom doesn't believe my beta is that small." The text that arrived about 10:30am while I was in my office.

Her mom? Amy was discussing our arrangement with her mom? That's crazy. Turns out her mom was one year younger than me as well.

"Hurry up Rickie! I don't expect to wait when I give you instruction." Another text popped up as I was contemplating the previous one.

"Yes ma'am. Sorry." I quickly responded. Then I opened my pants and pushed my panties down over my dick while I sat at my desk. I snapped a pic of my tiny soft penis and sent it off. "I hope it's okay that I'm soft right now."

"Holy shit! Lol. Thanks for that. I needed a good laugh but I'm worried about my mother. She's dying over here. She can't fathom that a grown man can have something so small. Lol. You're a good bitch!" Amy answered.

"Thank you mistress." I pictured her mother, probably still as beautiful as Amy, laughing while looking at the picture. Turning the phone sideways and dragging her fingers on the screen to enlarge it while comparing my penis to that of a toddler. That thought made me hard as a rock.

"Fuck it. I need you to leave work and get over here. My mom lives kinda close to your work anyway and I want her to see you in person." Amy told me.

"I'll need a few minutes to adjust my schedule before I can get out of here." I responded.

"So then do it pussy!" Amy berated me. She's really coming into her own with this domme stuff. "Here's the address: 547 Squire Lane. Hurry the fuck up."

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25 minutes later I was pulling in front of a very nice duplex condominium. I parked in the street and walked up to the door. Right before I could knock the door opened. Amy and a very sexy older woman, her mother I presumed, were standing in the door. Older than Amy, not me.

"Strip down to your panties right now and then you may enter the house." Amy said.

I looked around at the neighbors to see if anyone was outside.

"Did I fucking stutter?" Amy snapped her fingers at me.

"No mistress. Sorry mistress." I answered as I began disrobing.

"He's handsome Amy. Where did you find him? Nice body too. This can't be the owner of that tiny dickie in the picture." The older woman said.

"He came into the store the other day. He wanted to show me his little dick so bad. Now I own his sissy ass!" Amy explained.

I stood on the porch in nothing but a pair of lavender French cut lacy panties. I held my clothes folded up under my arm. My dick was rock hard as I waited for Amy to allow me to enter the home.

"Come on in sissy." Amy said as she turned and walked away into the house.

Her mother stepped to one side and held the door as I walked in. She smacked my ass as I passed her and said, "Nice ass bitch. Go on into the living room."

I turned toward the living room and saw Amy already sitting on the couch. I heard the door close and lock behind me. "Set your clothes on that table." Amy said pointing to a console table still in the foyer. "Then come and stand in front of me."

I set my clothes on the table and walked over to stand in front of my mistress. Her mother joined her on the couch and both gazed directly at my crotch.

"Drop the panties sissy!" Her mother said.

"Yes um...yes ma'am." I said nervously not knowing what to call her.

"You will address me as Miss Melanie. Will that be a problem tiny?" Amy's mother asked.

"No ma'am. I mean no Miss Melanie." I humbly responded.

"Are trying to get punished?" Amy broke in. "You just do whatever the fuck anyone tells you to? You feel the need to disrespect me right in front of my face? So you don't want to be my cuck bitch anymore? Now my mother owns you?" Amy drilled me.

"No mistress. I'm sorry mistress. I won't make that mistake again ma'am. I just didn't want to disrespect your mother. I don't want anyone else to own me mistress." I genuinely apologized. "I am yours to use ma'am."

"You will pay for that one day motherfucker but for now just drop those panties." Amy had gotten really good at this. I felt like a school boy being chastised by a sexy perverted teacher. What an erotic feeling!

So I put an index finger inside the waist of my panties on each side and pushed them down to my ankles. When I stood back up Miss Melanie busted out laughing.

"What the fuck is that?" She asked through her guffawing. "Even hard you're pathetic?" She said as she squeezed my solid little erection. "Not much bigger than the soft picture you sent us."

"I told you!" Amy shouted. "And he loves being my little dick sissy too! Don't you plaything?" Her voice went from jubilee to stern.

"Yes mistress. I love being humiliated and owned by you." I chanted out like an army cadet answering his drill Sargent.

Miss Melanie reached out and grabbed my small tight nut sack and stretched it down. "Even your balls are small. Maybe I can help with that." She had both hands pulling my sack down with complete disregard of my feelings about it.

I had never enjoyed my balls being touched, played with, or even sucked during oral. They have always been very sensitive so I've rejected any sexual contact to them over the years. But to be honest this uncomfortable slight pain I was feeling now was actually arousing. My small dick was pulsating as the blood gorged inside it.

"Here ma, use this hair tie to hold his balls down." Amy said handing her mother a black rubber band type pony tail tie.

So Miss Melanie held pulled both of my balls down with one hand and snapped the hair tie onto the top of my sack. Then she pulled on it and doubled it over and let the other half snap around the first part. My balls pushed down and elongated my sack and made the skin on my scrotum smooth. Yes it was painful and yes it was extremely pleasurable.

"That might help you keep from cumming in under 30 seconds too." Amy giggled.

Amy's mother put her fist on my penis. The head of my small dick barely poked out over her thumb and index finger. "You can't even jack off a dick this size!" She blurted out.

"He uses just his thumb and first two fingers when he jacks off. Show her Rickie." Amy commanded.

So I put my thumb and first two fingers on my cock as if I were going to jack off. I couldn't dare begin to stroke myself though for fear that I would cum right away. So I ever so slightly made the motion without really touching my penis. I reached down with my other hand and felt my stretched out ball sack but quickly pulled away because it felt so good.

"What's the matter sissy? Afraid you're going to cum?" Miss Melanie said grabbing my dick in her thumb and index finger. She slid her fingers back and forth on my short shaft while I winced and pulled away. She smacked my balls with her free hand and picked up the pace stroking me and dared me to cum. "You're so fucking pathetic. You can't even hold your cum! I've been with men that I had to work my ass off to get them to cum. And you better not pull away from me again and dam sure better not cum without permission or you're going to get fucking punished!" She degraded me with a smile as I tip toed on the edge of orgasm.

"Rickie, I thought you wanted to please me? Don't you like me? Are you trying to embarrass me in front of my mother?" Amy piled on.

"I do want to please you mistress. I love you mistress. I would never want to embarrass you ma'am." I apologized sincerely. I was in literal ecstasy at the moment but having to listen to both women and process my apology actually helped keep me from cumming. Also, the sting from Miss Melanie smacking my nut sack aided in delaying my orgasm.

"Maybe this will help." Mistress Amy said as she snapped another hair tie around the base of the shaft of my small wiener. "Dam I'm going to have to fold this over three or four times on your skinny dick!" Amy said doubling the hair tie over a couple times to tighten up my homemade cock ring.

"Thank you mistress." I expressed my gratitude.

There I stood in front of my new mistress and her sexy mother with my panties around my ankles and 2 hair ties cinched around my dick and balls. Miss Melanie had stopped stroking me, stood up and looked me directly in the eyes, and without a word walked out of the room. I looked at Amy to see her smiling as her mother left the room.

"I need to cum." Mistress Amy informed me as she stood up and pushed her leggings down to reveal her perfectly manicured vagina. Her pussy was beautiful. The lips weren't hanging out loose and yet they weren't completely cover by her outer labia. After kicking her leggings off her feet she laid back into the couch with her legs spread wide and said very firmly, "EAT!"

Being submissive and having a small dick I have always been very fond of performing cumninglingus. I immediately dropped to my knees almost tripping on the panties that still held my ankles close together. I buried my face between my mistress's legs and breathed in her sweet scent. I began to lick her out labia from bottom to top and then dipped my tongue into her entrance.

"There you go sissy. That's it. You eat pussy like a woman!" Amy was gyrating her pelvis while holding her legs out to each side. She is incredibly flexible. I appreciated the compliment too since I assume women eat pussy very good.

I continued expertly sucking, licking, and kissing my mistress's gorgeous pussy. My little dick and balls still excited and engorged from the hair ties that were tight around them. On my knees I held myself balanced with one hand on the floor and lightly petted the small patch of pubic hair above Amy's pussy with the other. I felt shudders in her pelvic area as she pulled my hair to bring my face deeper into her honey hole.

Mistress Amy and her mother must have communicated while I was buried in my owners luscious hole. Suddenly Amy's legs closed around my head in a tight scissor while Miss Melanie simultaneously pushed something cool and wet inside my exposed ass.

My natural reaction was to pull away and see what was happening but the legs wrapped tightly around my head didn't allow that. I felt a hard slap on my ass and heard Amy's mother say, though muffled from my ears being covered by creamy thighs, "wiggle that ass sissy!"

While struggling to breath and remain balanced I wiggled my ass as best I could to the repeated smacks. Whatever was inside my ass just sat there. Miss Melanie was not pushing it in and out. Mistress continued to cum several times as my face and her vagina became a soaking wet mess.

"Mom you have to have him eat your pussy. He's actually really good!" Amy told her mother.

"With a tiny dick like that you'd have to be good at something to land a wife." Miss Melanie observed.

Amy's legs suddenly released from around my head but I continued to lap at her lovely pussy until she told me to stop. I sat back on my heels like a puppy waiting to obey my next instructions. Mistress stood up and let Miss Melanie take her place. I don't know if vagina structure is genetic but her lovely pussy looked just like her daughter's. Without hesitation I leaned forward to serve her when a felt a smack across my face.

"Did someone tell you to eat sissy?" Amy shouted.

"No mistress." I cowered.

Miss Melanie spread her legs as wide as her daughter had a few minutes ago and tilted her pelvis up to give me a perfect view of not only her beautiful vagina but her tight pink asshole as well. "Don't forget the back door when you're down there sissy!" She said as she pulled my head forward.

I began to eagerly lick her asshole while my nose wiggled inside her pussy lips. I was met with immediate verbal reinforcement. "Oh that's very good. You like that asshole don't you sissy?"

"Yes Miss Melanie," I mumbled without missing a tongue lash.

Miss Melanie pushed my head away and flipped over so she was on her knees atop the couch. She spread her knees which also parted her ass cheeks and gave me direct access to her gorgeous pink sphincter.

"Get that tongue in there sissy!" She commanded me.

As I leaned forward again and restarted licking her tasty asshole I felt a hand grabbing and pulling down on my tied balls.

"I'm trying to stretch them and make you look more like a man. I doubt that'll happen though." Mistress Amy said. At the same time she was putting pressure on the object that was buried in my own ass. "Sissies like getting things put in their ass don't they?" She pondered out loud.

Miss Melanie was reaching under and rubbing her clit back and forth as I licked and tongue fucked her ass. She was pushing back into my face so much it felt like her full weight was resting on me. I felt her body shake and wriggle a couple times as she orgasmed hard.

"This little dick sissy is going to be fun to have around Amy." Miss Melanie told her daughter. "I hope you share him generously."

I loved being talked about like a piece of property. Especially as I knelt there naked except for the panties still around my ankles, with my balls and cock tied, my face glazed with female cum, and an unknown object buried in my ass.

Mistress and Miss Melanie left the room without instructing me further. I stayed on my knees waiting. I looked down at my small penis which was purple from the homemade cock ring placed at the base. My balls weren't discolored but looked bigger than I had ever seen them as they stretched out my sack. I wanted to touch myself so bad but I knew better than to do that without being told.

"Stand up bitch." I heard Mistress Amy behind me. "And turn around."

I stood up slowly while clenching my ass being sure to keep the foreign object in place. Then I shuffled my feet around being sure to keep my panties in place. Amy had gotten dressed.

"Pull that tie off your clit." Amy directed referencing my little dick. I noticed now that she had a flesh tone dildo in her hand. I wondered if that was similar to what was still buried in my ass.

"You're going to jack off and cum on this dildo. Then you're going to suck and lick your cum off of it. If one drop lands anywhere else or drips off you will clean that with your tongue as well." Amy instructed me as her mother walked back in the room after having freshened up.

After handing me the dildo both sexy ladies sat down to watch the show. I held the dildo in my left hand and put my thumb and index finger on my stubby shaft. I was afraid that I would shoot my load so hard that I'd miss the dildo all together and spend a half hour searching for splatters of cum throughout the room. After a few strokes I was ready to release my seed.

"Dam that dick is pathetic!" Miss Melanie reiterated. "It's like a miniature version of a real one."

"Watch how much he cums though." Mistress Amy added having seen my huge loads twice now.

At that I began shooting my milk onto the dildo in my hand. I used my hand as a wall to block any cum from shooting all over. I deposited possibly the largest amount of seed I'd ever shot onto the jelly cock and my hand. My orgasm seemed to last forever.

"Okay sissy. This isn't about you. We want to see you suck that cock now!" Mistress Amy yelled.

I wiped as much of the cum from my hand as possible on the dildo adding to the copious amount on it already. I tilted my head back held the cock toy up over my open mouth with the head pointing down and let the abundant cum drip down into my mouth.

"You like eating cum don't you faggot?" Miss Melanie shouted.

"Don't you fucking miss a drop of that salty treat queer!" Amy preliminarily scolded me.

After the initial overflow of cum dropped on to my tongue I brought the head of the dick to my lips and pushed it as deep as I could in my mouth. I couldn't take the entire length. The dildo was about 7" long and although I've sucked a cock this big before, a real one is very different from a sex toy.

"He's an experienced cock sucker too I see!" Miss Melanie said aloud. "That's good to know."

I sucked the cock toy like a pro putting on a good show for the ladies even after I had cleaned my jizz off completely. Being a closet cock sucker I had eliminated my gag reflex in the past so I pushed the dick all the way into my throat. By now my own little dick had softened and shrunk to its normal prepubescent size, looking even sillier with my balls still enlarged from the hair tie around them.

"Okay fag. Next time we'll see if we can provide a real cock for you to suck." Amy said to my surprise. "Go clean yourself up and get the fuck out of here. And the plug stays in for now."

"Yes mistress. Thank you for letting me cum mistress." I sounded like such a submissive sissy. So it was a butt plug that was pushed into my ass. I was worried about it falling out this whole time but they are made with a contour to help them stay in.

I dashed off to the rest room and cleaned up. Washed my glazed face and wiped the excess lube off my ass. Miss Melanie had glopped it on when she put the plug in. When I returned Mistress Amy was standing in the foyer with the door open and reminded me that I am to get dressed on the porch. I grabbed my pile of clothes and walked out the door. The door slammed behind me without a good bye.

I quickly got dressed and walked out to my car. A few neighbors were outside but I'm pretty sure no one saw me in my panties a few seconds previous. As I drove away I felt an aching in my dick and balls from the light abuse they had been through. I felt a little guilt too. If only my wife was into this type of fetish I wouldn't seek it out elsewhere.

My phone alerted to a text and at the next stop sign I lifted it up to see who it was from.

"I was very satisfied with your behavior today sissy. You will be rewarded soon. You may remove the anal plug when you get home. Wash it and keep it handy as you will insert it again upon my command."